GB1114113A - Improvements in or relating to prolines and the manufacture thereof - Google Patents
Improvements in or relating to prolines and the manufacture thereofInfo
- Publication number
- GB1114113A GB1114113A GB54342/67A GB5434267A GB1114113A GB 1114113 A GB1114113 A GB 1114113A GB 54342/67 A GB54342/67 A GB 54342/67A GB 5434267 A GB5434267 A GB 5434267A GB 1114113 A GB1114113 A GB 1114113A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- proline
- tosyl
- keto
- prolines
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 235000013930 proline Nutrition 0.000 title 1
- 150000003148 prolines Chemical class 0.000 title 1
- -1 1-substituted-4-keto-prolines Chemical class 0.000 abstract 3
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- JMJMJDNHVXYAOC-DTIOYNMSSA-N (2s)-4-hydroxy-1-[(4-nitrophenyl)methoxycarbonyl]pyrrolidine-2-carboxylic acid Chemical compound C1C(O)C[C@@H](C(O)=O)N1C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 JMJMJDNHVXYAOC-DTIOYNMSSA-N 0.000 abstract 1
- MHSGOABISYIYKP-UHFFFAOYSA-N (4-nitrophenyl)methyl carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(COC(Cl)=O)C=C1 MHSGOABISYIYKP-UHFFFAOYSA-N 0.000 abstract 1
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000003946 cyclohexylamines Chemical class 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 229960002591 hydroxyproline Drugs 0.000 abstract 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 abstract 1
- 238000007070 tosylation reaction Methods 0.000 abstract 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Saccharide Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Novel compounds of the formula <FORM:1114113/C2/1> (wherein R is an organic radical removable by catalytic hydrogenolysis and R1 is H or C1- 11 alkyl) and the D-isomers thereof are prepared by treating the corresponding 1-substituted-4-keto-prolines with a Wittig reagent (an alkylidenetriphenylphosphorane). R may be, for example, triphenylmethyl, benzyl, p-nitrobenzyl, tosyl, a benzyloxycarbonyl group in which the benzene ring may be para-substituted by nitro, methoxy, chloro or bromo, a phenyloxycarbonyl or p-(C1- 4 alkyl)-phenyloxycarbonyl group, or allyloxycarbonyl. Examples are given and cyclohexylamine salts of some of the products are described. 4-Keto-1-tosyl-L-proline is prepared by oxidation of 4-hydroxyl-1-tosyl-L-proline, itself prepared by N-tosylation. 1 - p - Nitrocarbobenzoxy - 4 - keto - L - proline (dicyclohexylamine salt also described) is prepared by oxidation of 1-p-nitrocarbobenzoxy-4-hydroxyproline (dicyclohexylamine salt also described), prepared in turn from 4-hydroxy-L-proline and p-nitrocarbobenzoxychloride.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US375324A US3301871A (en) | 1964-06-15 | 1964-06-15 | Novel 1, 4-dialkylprolines, derivatives thereof and process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1114113A true GB1114113A (en) | 1968-05-15 |
Family
ID=23480433
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB54344/67A Expired GB1114115A (en) | 1964-06-15 | 1965-05-25 | Improvements in or relating to antibiotics and the manufacture thereof |
| GB22157/65A Expired GB1114112A (en) | 1964-06-15 | 1965-05-25 | Improvements in or relating to prolines and the manufacture thereof |
| GB54342/67A Expired GB1114113A (en) | 1964-06-15 | 1965-05-25 | Improvements in or relating to prolines and the manufacture thereof |
| GB54343/67A Expired GB1114114A (en) | 1964-06-15 | 1965-05-25 | Improvements in or relating to prolines and the manufacture thereof |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB54344/67A Expired GB1114115A (en) | 1964-06-15 | 1965-05-25 | Improvements in or relating to antibiotics and the manufacture thereof |
| GB22157/65A Expired GB1114112A (en) | 1964-06-15 | 1965-05-25 | Improvements in or relating to prolines and the manufacture thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB54343/67A Expired GB1114114A (en) | 1964-06-15 | 1965-05-25 | Improvements in or relating to prolines and the manufacture thereof |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3301871A (en) |
| CH (1) | CH473801A (en) |
| DE (1) | DE1620602A1 (en) |
| FR (1) | FR1451315A (en) |
| GB (4) | GB1114115A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6703950B2 (en) | 2014-02-20 | 2020-06-03 | アーケマ・インコーポレイテッド | Method and system for producing acrylic acid |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3086912A (en) * | 1961-07-03 | 1963-04-23 | Upjohn Co | Antibiotic lincolnensin and method of production |
-
1964
- 1964-06-15 US US375324A patent/US3301871A/en not_active Expired - Lifetime
-
1965
- 1965-05-25 GB GB54344/67A patent/GB1114115A/en not_active Expired
- 1965-05-25 GB GB22157/65A patent/GB1114112A/en not_active Expired
- 1965-05-25 GB GB54342/67A patent/GB1114113A/en not_active Expired
- 1965-05-25 GB GB54343/67A patent/GB1114114A/en not_active Expired
- 1965-06-11 CH CH813265A patent/CH473801A/en not_active IP Right Cessation
- 1965-06-11 DE DE1965U0011802 patent/DE1620602A1/en active Pending
- 1965-06-14 FR FR20743A patent/FR1451315A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3301871A (en) | 1967-01-31 |
| DE1620602A1 (en) | 1970-02-12 |
| GB1114112A (en) | 1968-05-15 |
| GB1114115A (en) | 1968-05-15 |
| GB1114114A (en) | 1968-05-15 |
| FR1451315A (en) | 1966-09-02 |
| CH473801A (en) | 1969-06-15 |
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